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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Silybin a,b (mixture), 802918-57-6, Silybin (a+b), (2r,3r)-3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one, Legalon, Silibin

Molecular Formula

C₂₅H₂₂O₁₀

Molecular Weight

482.4 g/mol

InChI Key

SEBFKMXJBCUCAI-DBMPWETRSA-N

A mixture of flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum. It consists primarily of silybin and its isomers, silicristin and silidianin. Silymarin displays antioxidant and membrane stabilizing activity. It protects various tissues and organs against chemical injury, and shows potential as an antihepatoxic agent.

1 2D Structure

Silymarin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R)-3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one

2.1.2 InChI

InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20?,23-,24?,25+/m0/s1

2.1.3 InChI Key

SEBFKMXJBCUCAI-DBMPWETRSA-N

2.1.4 Canonical SMILES

COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O

2.1.5 Isomeric SMILES

COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 2,3 Dehydrosilybin

2. 2,3-dehydrosilybin

3. Alepa Forte

4. Alepa-forte

5. Ardeyhepan

6. Cefasilymarin

7. Durasilymarin

8. Hepa Loges

9. Hepa Merz Sil

10. Hepa-loges

11. Hepa-merz Sil

12. Hepabesch

13. Hepar Pasc

14. Hepar-pasc

15. Heparsyx

16. Heplant

17. Lagosa

18. Legalon Forte

19. Silibin

20. Silibinin

21. Silibinin A

22. Silibinin B

23. Silybin A

24. Silybin B

25. Silybinin

26. Carsil

27. Karsil

28. Legalon

29. Silimarin

30. Silymarin

2.2.2 Depositor-Supplied Synonyms

1. Silybin A,b (mixture)

2. 802918-57-6

3. Silybin (a+b)

4. (2r,3r)-3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one

5. Legalon

6. Silibin

7. Silliver

8. Silybine

9. Silymarin

10. Chembl9509

11. Silibinin A-silibinin B Mixt.

12. Schembl14270800

13. Schembl22398934

14. Hy-n0779a

15. Cs-0138778

16. S0508

17. E80721

18. Silybin (mixture Of Silybin A And B) 100 Microg/ml In Acetonitrile

19. (2r,3r)-2,3-dihydro-3,5,7-trihydroxy-2-[3-(4-hydroxy-3-methoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-yl]-4h-1-benzopyran-4-one

20. 2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl)benzodioxine

2.3 Create Date

2005-08-09

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₂₂O₁₀
Molecular Weight	482.4 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	4
Exact Mass	482.12129689 g/mol
Monoisotopic Mass	482.12129689 g/mol
Topological Polar Surface Area	155 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	750
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

Protective Agents

Synthetic or natural substances which are given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent. (See all compounds classified as Protective Agents.)

4.2 ATC Code

A - Alimentary tract and metabolism

A05 - Bile and liver therapy

A05B - Liver therapy, lipotropics

A05BA - Liver therapy

A05BA03 - Silymarin

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API Reference Price

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